Abstract: This paper, based on an upcoming CRC for Remote Economic Participation (CRC-REP) research project—‘Pathways to Employment’—will canvas the proposition that mobile technology can be used as an effective vehicle for vocational learning in remote communities. This proposition in itself is not new and indeed there are a number of examples in the literature that demonstrate the possibilities of mobile and emerging digital technologies in remote Aboriginal and Torres Strait Islander communities in Australia and indigenous communities elsewhere in the world. However, the application of technologies in vocational learning is often applied to the delivery of mainstream training packages for mainstream employment outcomes. The ‘Pathways to Employment’ research project will consider pathways from a different starting point than many other research projects, which take as a given, the traditional notion of pathways to employment—typically linear, mainstream oriented and driven—with all the mainstream assumptions that go along with this notion of ‘pathway’. This paper foregrounds the research with a consideration of the literature on effective application of digital technologies in vocational learning and the intersection between these technologies, vocational learning and their fit within a pathway. The philosophical underpinnings behind the pathways construct are examined and questioned as to their fit within a remote Aboriginal and Torres Strait Islander context. The paper suggests that the reason the apparently successful applications of digital technologies in remote VET programs work is because of their fit with Aboriginal and Torres Strait Islander ontologies, epistemologies and axiologies. The data collection phase of the research project will commence later in 2012. However, ahead of the research itself, this paper poses several questions that will form the basis of one part of the ‘Pathways’ project. These will include questions about the scope of using technology for ‘Aboriginally’ constructed vocational training products and processes that fit the breadth of livelihood aspirations in remote communities.